Methods to refine cannabinoids

ABSTRACT

This disclosure generally relates to gas-phase methods to simultaneously purify and decarboxylate cannabinoids in about two seconds, which are about 100-10,000 times more efficient than conventional purification and decarboxylation strategies. The methods also recover thermolabile cannabinoids such as cannabigerol at significantly higher yields than conventional methods.

CROSS-REFERENCE TO RELATED APPLICATIONS

This patent document claims priority to U.S. Provisional PatentApplication No. 62/971,742, filed Feb. 7, 2020, which is incorporated byreference in its entirety.

BACKGROUND

Industrial hemp contains cannabinoid carboxylic acids that can bedecarboxylated and purified to produce refined cannabinoid products. Thelegitimate industry that manufactures cannabinoids at scale is nascent,and methods to decarboxylate and purify cannabinoids that displayeconomies of scale are desirable.

SUMMARY

This disclosure generally relates to gas-phase methods to simultaneouslypurify and decarboxylate cannabinoids in about 2 seconds, which is about100-10,000 times more efficient than conventional purification anddecarboxylation strategies. The methods also recover thermolabilecannabinoids such as cannabigerol at significantly higher yields thanconventional methods. Comprehensive descriptions of the methods aredisclosed in the detailed description that follows and published in U.S.Pat. Nos. 10,669,248 and 10,822,320, which are incorporated by referencein their entirety.

DETAILED DESCRIPTION

Various aspects of the disclosure relate to a method tochemically-modify a cannabinoid, comprising: providing a compositioncomprising the cannabinoid, wherein the cannabinoid comprises a carboxylgroup, and the cannabinoid is in a liquid phase or a solid phase;contacting the composition with sufficient energy to convert thecannabinoid into carbon dioxide and a modified cannabinoid in a gasphase; contacting the modified cannabinoid with a heat sink to condensethe modified cannabinoid into a condensed cannabinoid in a liquiddistillate; and collecting the liquid distillate. Cannabinoids thatcomprise a carboxyl group are either carboxylic acids or carboxylates.

Various aspects of the disclosure relate to a method to purify acannabinoid from a non-volatile chemical species, comprising: providinga composition comprising the cannabinoid and the non-volatile chemicalspecies, wherein both the cannabinoid and the non-volatile chemicalspecies are in a liquid phase or a solid phase; contacting thecomposition with sufficient energy to convert the cannabinoid in theliquid phase or the solid phase into a vaporized cannabinoid in a gasphase without vaporizing the non-volatile chemical species; separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species; contacting the vaporized cannabinoid with a heat sinkto condense the vaporized cannabinoid into a condensed cannabinoid in aliquid distillate; and collecting the liquid distillate.

U.S. Patent Application Publication No. 2016/0038437 A1 ('437application) and its international counterparts disclose failed attemptsto perform commercially-viable gas-phase decarboxylation andpurification. The '437 application states, “The rate of decarboxylationis a product of temperature and time. At 145° C. 95% of cannabinoid acidis decarboxylated in approximately 30 minutes.” FIGS. 6-10 of the '437application show that gas chromatography (“GC”) was used to measurecannabinoid decarboxylation, but gas chromatography is known to performquantitative decarboxylation as evidenced by near-completedecarboxylation of the starting material in FIGS. 6-10. Table 2 andFIGS. 6-10 indicate that the extraction was incomplete because anundisclosed amount of cannabinoids were left behind in the “spent herb.”Table 2 also indicates that the method resulted in significant amountsof the cannabinoid oxidation product cannabinol (“CBN”) and the thermaldegradation product delta8-tetrahydrocannabinol (“Δ8-THC”).

The '437 application erred in the presumption that temperature should beoptimized to purify and decarboxylate cannabinoids in the gas phase: “Itis therefore preferred to use a temperature which is as low as possiblein order to minimise thermal-oxidative degradation and thermalisomerisation of Δ9-THC.” The instant disclosure teaches that energytransfer should be optimized to purify and decarboxylate cannabinoids inthe gas phase. Optimizing energy transfer independently from temperatureallows (1) extraction times of about 2 seconds rather than“approximately 30 minutes,” (2) actual decarboxylation of greater than95 percent rather than hypothetical decarboxylation of 95 percent, (3)demonstrable yields of greater than 90 percent rather than yields thatare too low to report, and (4) minimal conversion of cannabinoids intocannabinol rather than significant conversion into cannabinol. Theinstant disclosure also describes a continuous process that improvesupon the batch process of the '437 application.

In some embodiments, the sufficient energy is no greater than 100kilojoules per gram of the composition. In some specific embodiments,the sufficient energy is at least 500 joules and no greater than 100kilojoules per gram of the composition. In some very specificembodiments, the sufficient energy is at least 2 kilojoules and nogreater than 50 kilojoules per gram of the composition. Any feature setforth in a preceding sentence of this paragraph is combinable with anyfeature set forth in paragraphs 10-36 and can depend from either of theembodiments set forth in paragraphs 04 and 05.

In some embodiments, the sufficient energy is no greater than 0.04kilowatt hours per gram of the composition. In some specificembodiments, the sufficient energy is at least 0.0003 and no greaterthan 0.04 kilowatt hours per gram of the composition. In some veryspecific embodiments, the sufficient energy is at least 0.0005 and nogreater than 0.02 kilowatt hours per gram of the composition. Anyfeature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 10-36 and can depend from either of the embodiments set forthin paragraphs 04 and 05.

In some embodiments, the sufficient energy is provided at a rate of nogreater than 100 kilowatts of power per gram of the composition for aduration of no greater than 60 seconds. In some specific embodiments,the sufficient energy is provided at a rate of at least 1 kilowatt andno greater than 100 kilowatts of power per gram of the composition for aduration of at least 200 milliseconds and no greater than 20 seconds.Any feature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 08, 09, and 11-36 and can depend from either of theembodiments set forth in paragraphs 04 and 05.

In some embodiments, the composition comprises the cannabinoid at aconcentration of at least 0.1 percent by mass. In some specificembodiments, the composition comprises the cannabinoid at aconcentration of at least 5 percent by mass. In some very specificembodiments, the composition comprises the cannabinoid at aconcentration of at least 10 percent by mass. Any feature set forth in apreceding sentence of this paragraph is combinable with any feature orcombination of features set forth in paragraphs 08-10 and 12-36 and candepend from either of the embodiments set forth in paragraphs 04 and 05.Higher concentrations of cannabinoids improve energy transfer.

In some embodiments, the composition has a surface-area-to-volume ratioof greater than 100 per meter (m⁻¹). In some specific embodiments, thecomposition has a surface-area-to-volume ratio of greater than 500 permeter. In some very specific embodiments, the composition has asurface-area-to-volume ratio of greater than 1000 per meter. Any featureset forth in a preceding sentence of this paragraph is combinable withany feature or combination of features set forth in paragraphs 08-11 and13-36 and can depend from either of the embodiments set forth inparagraphs 04 and 05. Greater surface-area-to-volume improves energytransfer.

In some embodiments, the method comprises grinding the composition to asurface-area-to-volume ratio of greater than 100 per meter. In someembodiments, the method comprises grinding the composition to asurface-area-to-volume ratio of greater than 100 per meter to produceparticles of the composition. In some specific embodiments, the methodcomprises grinding the composition to a surface-area-to-volume ratio ofgreater than 500 per meter. In some specific embodiments, the methodcomprises grinding the composition to a surface-area-to-volume ratio ofgreater than 500 per meter to produce particles of the composition. Insome very specific embodiments, the method comprises grinding thecomposition to a surface-area-to-volume ratio of greater than 1000 permeter. In some very specific embodiments, the method comprises grindingthe composition to a surface-area-to-volume ratio of greater than 1000per meter to produce particles of the composition. Any feature set forthin a preceding sentence of this paragraph is combinable with any featureor combination of features set forth in paragraphs 08-12 and 14-36 andcan depend from either of the embodiments set forth in paragraphs 04 and05. Smaller particle size allows the composition to be suspended in agas phase, which improves energy transfer.

In some embodiments, the method comprises suspending a particle of thecomposition in the gas phase. In some specific embodiments, the methodcomprises suspending a particle of the composition in the gas phase,wherein the particle comprises the cannabinoid. In some very specificembodiments, the method comprises suspending a particle of thecomposition in the gas phase, wherein the particle comprises thecannabinoid, and the method comprises contacting the cannabinoid withthe sufficient energy while the particle is suspended in the gas phase.In some embodiments, the method comprises suspending a droplet of thecomposition in the gas phase. In some specific embodiments, the methodcomprises suspending a droplet of the composition in the gas phase,wherein the droplet comprises the cannabinoid. In some very specificembodiments, the method comprises suspending a droplet of thecomposition in the gas phase, wherein the droplet comprises thecannabinoid, and the method comprises contacting the cannabinoid withthe sufficient energy while the droplet is suspended in the gas phase.Any feature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 08-13 and 15-36 and can depend from either of the embodimentsset forth in paragraphs 04 and 05. Suspending a particle or droplet inthe gas phase improves energy transfer.

In some embodiments, the method comprises suspending particles of thecomposition in the gas phase. In some specific embodiments, the methodcomprises suspending particles of the composition in the gas phase,wherein the particles comprise the cannabinoid. In some very specificembodiments, the method comprises suspending particles of thecomposition in the gas phase, wherein the particle comprises thecannabinoid, and the method comprises contacting the cannabinoid withthe sufficient energy while the particles are suspended in the gasphase. In some embodiments, the method comprises suspending droplets ofthe composition in the gas phase. In some specific embodiments, themethod comprises suspending droplets of the composition in the gasphase, wherein the droplets comprise the cannabinoid. In some veryspecific embodiments, the method comprises suspending droplets of thecomposition in the gas phase, wherein the droplets comprise thecannabinoid, and the method comprises contacting the cannabinoid withthe sufficient energy while the droplets are suspended in the gas phase.Any feature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 08-14 and 16-36 and can depend from either of the embodimentsset forth in paragraphs 04 and 05. Suspending particles or droplets inthe gas phase allows continuous operation.

In some embodiments, the method comprises directing the compositionalong a heated path having a length of at least 100 millimeters, whereinthe composition is contacted with the sufficient energy in the heatedpath. In some specific embodiments, the method comprises directing thecomposition along a heated path having a length of at least 1 meter,wherein the composition is contacted with the sufficient energy in theheated path. In some very specific embodiments, the method comprisesdirecting the composition along a heated path having a length of atleast 4 meters, wherein the composition is contacted with the sufficientenergy in the heated path. Any feature set forth in a preceding sentenceof this paragraph is combinable with any feature or combination offeatures set forth in paragraphs 08-15 and 17-36 and can depend fromeither of the embodiments set forth in paragraphs 04 and 05. Directingthe composition along a heated path allows precise control of energytransfer because dwell time in the heated path correlates with energytransfer. Path length correlates with dwell time.

In some embodiments, the method comprises directing particles of thecomposition along a heated path having a length of at least 100millimeters, wherein the composition is contacted with the sufficientenergy in the heated path. In some specific embodiments, the methodcomprises directing particles of the composition along a heated pathhaving a length of at least 1 meter, wherein the composition iscontacted with the sufficient energy in the heated path. In some veryspecific embodiments, the method comprises directing particles of thecomposition along a heated path having a length of at least 4 meters,wherein the composition is contacted with the sufficient energy in theheated path. Any feature set forth in a preceding sentence of thisparagraph is combinable with any feature or combination of features setforth in paragraphs 08-16 and 18-36 and can depend from either of theembodiments set forth in paragraphs 04 and 05.

In some specific embodiments, the method comprises directing thecomposition along a heated path at a rate of at least 100 millimetersper minute. In some very specific embodiments, the method comprisesdirecting the composition along a heated path at a rate of at least 2meters per second. In some embodiments, the method comprises directingthe composition along a heated surface. In some specific embodiments,the method comprises directing the composition along a heated surface ata rate of at least 100 millimeters per minute. In some very specificembodiments, the method comprises directing the composition along aheated surface at a rate of at least 2 meters per second. Any featureset forth in a preceding sentence of this paragraph is combinable withany feature or combination of features set forth in paragraphs 08-17 and19-36 and can depend from either of the embodiments set forth inparagraphs 04 and 05. Directing the composition along a heated pathallows precise control of energy transfer because dwell time in theheated path correlates with energy transfer. The rate at which thecomposition travels through the heated path correlates with dwell time.

In some embodiments, the method comprises coating a heated surface withthe composition at a surface-area-to-volume ratio of the compositionthat is greater than 100 per meter. In some specific embodiments, themethod comprises coating a heated surface with the composition at asurface-area-to-volume ratio of the composition that is greater than 100per meter, and the method comprises contacting the cannabinoid with thesufficient energy while the composition is coated on the heated surface.In some specific embodiments, the method comprises coating a heatedsurface with the composition at a surface-area-to-volume ratio of thecomposition that is greater than 500 per meter. In some very specificembodiments, the method comprises coating a heated surface with thecomposition at a surface-area-to-volume ratio of the composition that isgreater than 500 per meter, and the method comprises contacting thecannabinoid with the sufficient energy while the composition is coatedon the heated surface. Any feature set forth in a preceding sentence ofthis paragraph is combinable with any feature or combination of featuresset forth in paragraphs 08-18 and 20-36 and can depend from either ofthe embodiments set forth in paragraphs 04 and 05.

In some embodiments, the method comprises contacting the compositionwith a heated gas having a temperature of at least 190 and no greaterthan 250 degrees Celsius. In some specific embodiments, the methodcomprises contacting the composition with a heated gas having atemperature of at least 205 and no greater than 235 degrees Celsius. Insome embodiments, the method comprises contacting the composition with aheated surface having a temperature of at least 190 and no greater than250 degrees Celsius. In some specific embodiments, the method comprisescontacting the composition with a heated surface having a temperature ofat least 205 and no greater than 235 degrees Celsius. Any feature setforth in a preceding sentence of this paragraph is combinable with anyfeature or combination of features set forth in paragraphs 08-19 and21-36 and can depend from either of the embodiments set forth inparagraphs 04 and 05.

In some embodiments, the composition comprises the cannabinoid and anon-volatile chemical species, and the method comprises both separatingthe modified cannabinoid in the gas phase from the non-volatile chemicalspecies and collecting the non-volatile chemical species. In somespecific embodiments, the composition comprises the cannabinoid and anon-volatile chemical species, and the method comprises both separatingthe modified cannabinoid in the gas phase from the non-volatile chemicalspecies and collecting the non-volatile chemical species, wherein theseparating occurs both (a) after converting the cannabinoid into thecarbon dioxide and the modified cannabinoid and (b) prior to contactingthe modified cannabinoid with the heat sink. Any feature set forth in apreceding sentence of this paragraph is combinable with any feature orcombination of features set forth in paragraphs 08-20, 23, 24, 26,28-33, and 35 and can depend from the embodiment set forth in paragraph04.

In some embodiments, the composition comprises the cannabinoid and thenon-volatile chemical species, and the method comprises both separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species and collecting the non-volatile chemical species,wherein the separating occurs both (a) after converting the cannabinoidinto the vaporized cannabinoid and (b) prior to contacting the vaporizedcannabinoid with the heat sink. Any feature set forth in a precedingsentence of this paragraph is combinable with any feature or combinationof features set forth in paragraphs 08-20, 23, 25, 27-32, 34, and 36 andcan depend from the embodiment set forth in paragraph 05.

In some very specific embodiments, the non-volatile chemical species iscellulose. In some very specific embodiments, the non-volatile chemicalspecies is chlorophyll. In some very specific embodiments, thenon-volatile chemical species is nucleic acid that comprises one or morenucleotide sequences that encode a geranyl-pyrophosphate-olivetolic acidgeranyltransferase. In some very specific embodiments, the non-volatilechemical species is protein that comprises one or more amino acidsequences that encode a geranyl-pyrophosphate-olivetolic acidgeranyltransferase. Any feature set forth in a preceding sentence ofthis paragraph is combinable with any feature or combination of featuresset forth in paragraphs 08-20, 22, and 24-36 and can depend from eitherof the embodiments set forth in paragraphs 05 and 21.

In some embodiments, the method comprises contacting the modifiedcannabinoid with the heat sink less than 240 seconds after contactingthe composition with the sufficient energy. In some specificembodiments, the method comprises contacting the modified cannabinoidwith the heat sink less than 60 seconds after contacting the compositionwith the sufficient energy. In some very specific embodiments, themethod comprises contacting the modified cannabinoid with the heat sinkless than 30 seconds after contacting the composition with thesufficient energy. Any feature set forth in a preceding sentence of thisparagraph is combinable with any feature or combination of features setforth in paragraphs 08-21, 23, 26, 28-33, and 35 and can depend from theembodiment set forth in paragraph 04. The methods of this disclosuredisplay markedly-improved efficiency relative to conventionaldecarboxylation, which takes about 30 minutes for boutique productionand several hours for production at scale.

In some embodiments, the vaporized cannabinoid is condensed into thecondensed cannabinoid less than 240 seconds after the cannabinoid isconverted into the vaporized cannabinoid. In some specific embodiments,the vaporized cannabinoid is condensed into the condensed cannabinoidless than 60 seconds after the cannabinoid is converted into thevaporized cannabinoid. In some very specific embodiments, the vaporizedcannabinoid is condensed into the condensed cannabinoid less than 30seconds after the cannabinoid is converted into the vaporizedcannabinoid. Any feature set forth in a preceding sentence of thisparagraph is combinable with any feature or combination of features setforth in paragraphs 08-20, 22, 23, 27-32, 34, and 36 and can depend fromthe embodiment set forth in paragraph 05.

In some embodiments, both contacting the composition with the sufficientenergy and condensing the modified cannabinoid into the condensedcannabinoid are performed in less than 240 seconds. In some specificembodiments, both contacting the composition with the sufficient energyand condensing the modified cannabinoid into the condensed cannabinoidare performed in less than 60 seconds. In some very specificembodiments, both contacting the composition with the sufficient energyand condensing the modified cannabinoid into the condensed cannabinoidare performed in less than 30 seconds. Any feature set forth in apreceding sentence of this paragraph is combinable with any feature orcombination of features set forth in paragraphs 08-21, 23, 24, 28-33,and 35 and can depend from the embodiment set forth in paragraph 04.

In some embodiments, each of (i) contacting the composition with thesufficient energy, (ii) separating the vaporized cannabinoid in the gasphase from the non-volatile chemical species, and (iii) contacting thevaporized cannabinoid with the heat sink are performed in a total timeof less than 240 seconds. In some specific embodiments, each of (i)contacting the composition with the sufficient energy, (ii) separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species, and (iii) contacting the vaporized cannabinoid withthe heat sink are performed in a total time of less than 60 seconds. Insome very specific embodiments, each of (i) contacting the compositionwith the sufficient energy, (ii) separating the vaporized cannabinoid inthe gas phase from the non-volatile chemical species, and (iii)contacting the vaporized cannabinoid with the heat sink are performed ina total time of less than 30 seconds. Any feature set forth in apreceding sentence of this paragraph is combinable with any feature orcombination of features set forth in paragraphs 08-20, 22, 23, 25,28-32, 34, and 36 and can depend from the embodiment set forth inparagraph 05.

In some embodiments, at least 75 percent of the cannabinoid is convertedinto the condensed cannabinoid per mole. In some specific embodiments,at least 85 percent of the cannabinoid is converted into the condensedcannabinoid per mole. In some very specific embodiments, at least 95percent of the cannabinoid is converted into the condensed cannabinoidper mole. Any feature set forth in a preceding sentence of thisparagraph is combinable with any feature or combination of features setforth in paragraphs 08-27 and 29-36 and can depend from either of theembodiments set forth in paragraphs 04 and 05. The yields obtainable bythe methods of this disclosure are generally superior to conventionalextraction methods performed at scale, for example, because combiningpurification and decarboxylation minimizes loss.

In some embodiments, the method comprises producing a liquid distillatethat comprises the condensed cannabinoid and cannabinol at a molar ratioof greater than 100:1. In some specific embodiments, the methodcomprises producing a liquid distillate that comprises the condensedcannabinoid and cannabinol at a molar ratio of greater than 200:1. Insome specific embodiments, the method comprises producing a liquiddistillate that comprises cannabinol at a concentration of no greaterthan 0.5 percent by mass. In some very specific embodiments, the methodcomprises producing a liquid distillate that comprises cannabinol at aconcentration of no greater than 0.2 percent by mass. Any feature setforth in a preceding sentence of this paragraph is combinable with anyfeature or combination of features set forth in paragraphs 08-28 and30-36 and can depend from either of the embodiments set forth inparagraphs 04 and 05. Conventional decarboxylation produces theoxidation product cannabinol. The methods of this disclosure minimizeoxidation by minimizing decarboxylation time.

In some embodiments, the method comprises producing a product from theliquid distillate, wherein the product comprises the condensedcannabinoid at a concentration of at least 50 percent by mass. In somespecific embodiments, the method comprises producing a product from theliquid distillate, wherein the product comprises the condensedcannabinoid at a concentration of at least 55 percent by mass. In somevery specific embodiments, the method comprises producing a product fromthe liquid distillate, wherein the product comprises the condensedcannabinoid at a concentration of at least 60 percent by mass. Anyfeature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 08-29 and 31-36 and can depend from either of the embodimentsset forth in paragraphs 04 and 05. The methods of this disclosuregenerally improve purity relative to conventional extraction methodsbecause the methods of this disclosure both distill cannabinoids duringdecarboxylation and minimize the production of oxidation product andthermal-degradation product impurities.

In some embodiments, the liquid distillate comprises ethanol, and themethod comprises evaporating the ethanol to produce a product. In somespecific embodiments, the liquid distillate comprises ethanol, and themethod comprises evaporating the ethanol to produce a product from theliquid distillate, wherein the product comprises the condensedcannabinoid at a concentration of at least 50 percent by mass. In somevery specific embodiments, the liquid distillate comprises ethanol, andthe method comprises evaporating the ethanol to produce a product fromthe liquid distillate, wherein the product comprises the condensedcannabinoid at a concentration of at least 55 percent by mass. In someeven more specific embodiments, the liquid distillate comprises ethanol,and the method comprises evaporating the ethanol to produce a productfrom the liquid distillate, wherein the product comprises the condensedcannabinoid at a concentration of at least 60 percent by mass. Anyfeature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 08-30 and 32-36 and can depend from either of the embodimentsset forth in paragraphs 04 and 05. Ethanol reduces viscosity to improvethe fluid dynamics of the liquid distillate. Improved fluid dynamicsallows pumping that enables continuous operation.

In some embodiments, the cannabinoid is cannabidiolic acid (CBDA;2,4-dihydroxy-3-(6-isopropenyl-3-methylcyclohex-2-enyl)-6-pentylbenzoicacid), and the condensed cannabinoid is cannabidiol (CBD;2-(6-isopropenyl-3-methylcyclohex-2-enyl)-5-pentylbenzene-1,3-diol). Insome embodiments, the cannabinoid is cannabidivarinic acid (CBDVA;2,4-dihydroxy-3-(6-isopropenyl-3-methylcyclohex-2-enyl)-6-propylbenzoicacid), and the condensed cannabinoid is cannabidivarin (CBDV;2-(6-isopropenyl-3-methylcyclohex-2-enyl)-5-propylbenzene-1,3-diol). Insome embodiments, the cannabinoid is tetrahydrocannabinolic acid (THCA;1-hydroxy-6,6,9-trimethylpentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acid), andthe condensed cannabinoid is tetrahydrocannabinol (THC;6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol).In some embodiments, the cannabinoid is tetrahydrocannabivarinic acid(THCVA; 1-hydroxy-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acid),and the condensed cannabinoid is tetrahydrocannabivarin (THC;6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol).In some embodiments, the cannabinoid is cannabigerolic acid (CBGA;3-geranyl-2,4-dihydroxy-6-pentylbenzoic acid), and the condensedcannabinoid is cannabigerol (CBG; 2-geranyl-5-pentylbenzene-1,3-diol).In some embodiments, the cannabinoid is cannabigerovarinic acid (CBGVA;3-geranyl-2,4-dihydroxy-6-propylbenzoic acid), and the condensedcannabinoid is cannabigerovarin (CBGV;2-geranyl-5-propylbenzene-1,3-diol). Any feature set forth in apreceding sentence of this paragraph is combinable with any feature orcombination of features set forth in paragraphs 08-31 and 33-36 and candepend from either of the embodiments set forth in paragraphs 04 and 05.

In some embodiments, the cannabinoid is cannabidiolic acid, and themodified cannabinoid and the condensed cannabinoid are both cannabidiol.In some embodiments, the cannabinoid is cannabidivarinic acid, and themodified cannabinoid and the condensed cannabinoid are bothcannabidivarin. In some embodiments, the cannabinoid istetrahydrocannabinolic acid, and the modified cannabinoid and thecondensed cannabinoid are both tetrahydrocannabinol. In someembodiments, the cannabinoid is tetrahydrocannabivarinic acid, and themodified cannabinoid and the condensed cannabinoid are bothtetrahydrocannabivarin. In some embodiments, the cannabinoid iscannabigerolic acid, and the modified cannabinoid and the condensedcannabinoid are both cannabigerol. In some embodiments, the cannabinoidis cannabigerovarinic acid, and the modified cannabinoid and thecondensed cannabinoid are both cannabigerovarin. Any feature set forthin a preceding sentence of this paragraph is combinable with any featureor combination of features set forth in paragraphs 08-21, 23, 24, 26,28-32, and 35 and can depend from the embodiment set forth in paragraph04.

In some embodiments, the cannabinoid is cannabidiolic acid, and thevaporized cannabinoid and the condensed cannabinoid are bothcannabidiol. In some embodiments, the cannabinoid is cannabidivarinicacid, and the vaporized cannabinoid and the condensed cannabinoid areboth cannabidivarin. In some embodiments, the cannabinoid istetrahydrocannabinolic acid, and the vaporized cannabinoid and thecondensed cannabinoid are both tetrahydrocannabinol. In someembodiments, the cannabinoid is tetrahydrocannabivarinic acid, and thevaporized cannabinoid and the condensed cannabinoid are bothtetrahydrocannabivarin. In some embodiments, the cannabinoid iscannabigerolic acid, and the vaporized cannabinoid and the condensedcannabinoid are both cannabigerol. In some embodiments, the cannabinoidis cannabigerovarinic acid, and the vaporized cannabinoid and thecondensed cannabinoid are both cannabigerovarin. In some embodiments,the cannabinoid, the vaporized cannabinoid, and the condensedcannabinoid are each cannabidiol. In some embodiments, the cannabinoid,the vaporized cannabinoid, and the condensed cannabinoid are eachcannabidivarin. In some embodiments, the cannabinoid, the vaporizedcannabinoid, and the condensed cannabinoid are eachtetrahydrocannabinol. In some embodiments, the cannabinoid, thevaporized cannabinoid, and the condensed cannabinoid are eachtetrahydrocannabivarin. In some embodiments, the cannabinoid, thevaporized cannabinoid, and the condensed cannabinoid are eachcannabigerol. In some embodiments, the cannabinoid, the vaporizedcannabinoid, and the condensed cannabinoid are each cannabigerovarin.Any feature set forth in a preceding sentence of this paragraph iscombinable with any feature or combination of features set forth inparagraphs 08-20, 22, 23, 25, 27-32, and 36 and can depend from theembodiment set forth in paragraph 05.

In some embodiments, the sufficient energy is sufficient to maintain anaverage reaction rate for the conversion of the cannabinoid into themodified cannabinoid over a period of time; the modified cannabinoid iscondensed at an average condensation rate for the condensation of themodified cannabinoid into the condensed cannabinoid over a concurrentperiod of time; the average condensation rate is no less than 50 percentof the average reaction rate; the average reaction rate is no less than50 percent of the average condensation rate; the period of time and theconcurrent period of time are chronologically identical; and the periodof time and the concurrent period of time are at least 200 millisecondsand no greater than 5 minutes. In some specific embodiments, thesufficient energy is sufficient to maintain an average reaction rate forthe conversion of the cannabinoid into the modified cannabinoid over aperiod of time; the modified cannabinoid is condensed at an averagecondensation rate for the condensation of the modified cannabinoid intothe condensed cannabinoid over a concurrent period of time; the averagecondensation rate is no less than 50 percent of the average reactionrate; the average reaction rate is no less than 50 percent of theaverage condensation rate; the period of time and the concurrent periodof time are chronologically identical; and the period of time and theconcurrent period of time are at least 200 milliseconds and no greaterthan 240 seconds. Any feature set forth in a preceding sentence of thisparagraph is combinable with any feature or combination of features setforth in paragraphs 08-21, 23, 24, 26, 28-32, and 33 and can depend fromthe embodiment set forth in paragraph 04. Harmonizing reaction rate withcondensation rate allows continuous operation.

In some embodiments, the sufficient energy is sufficient to maintain anaverage vaporization rate for the conversion of the cannabinoid into thevaporized cannabinoid over a period of time; the vaporized cannabinoidis condensed into the condensed cannabinoid at an average condensationrate for the condensation of the vaporized cannabinoid into thecondensed cannabinoid over a concurrent period of time; the averagecondensation rate is no less than 50 percent of the vaporization rate;the average vaporization rate is no less than 50 percent of the averagecondensation rate; the period of time and the concurrent period of timeare chronologically identical; and the period of time and the concurrentperiod of time are at least 200 milliseconds and no greater than 5minutes. In some specific embodiments, the sufficient energy issufficient to maintain an average vaporization rate for the conversionof the cannabinoid into the vaporized cannabinoid over a period of time;the vaporized cannabinoid is condensed into the condensed cannabinoid atan average condensation rate for the condensation of the vaporizedcannabinoid into the condensed cannabinoid over a concurrent period oftime; the average condensation rate is no less than 50 percent of thevaporization rate; the average vaporization rate is no less than 50percent of the average condensation rate; the period of time and theconcurrent period of time are chronologically identical; and the periodof time and the concurrent period of time are at least 200 millisecondsand no greater than 240 seconds. Any feature set forth in a precedingsentence of this paragraph is combinable with any feature or combinationof features set forth in paragraphs 08-20, 22, 23, 25, 27-32, and 34 andcan depend from the embodiment set forth in paragraph 05. Harmonizingvaporization rate with condensation rate allows continuous operation.

EXAMPLE Purification and Decarboxylation of Cannabinoids from USDAOrganic Industrial Hemp

The methods described in the detailed description were performed on 25tons of USDA organic industrial hemp to produce USDA organic certifiedhemp extracts that are sold online and in natural product grocersthroughout the United States. Third party ISO/IEC 17025 accreditedcannabinoid testing laboratories were engaged to measure cannabinoidconcentrations in the raw plant material, extracted plant material, andextract to support regulatory compliance, quality control, and valuationof the input and outputs. Measurements obtained on two different lots ofthe 25-ton production run are set forth in Tables 1 and 2. Thesemeasurements are disclosed for exemplary purposes, and they do not limitthe scope of the disclosure or any claim that matures from this patentdocument.

TABLE 1 Gas-Phase Purification and Decarboxylation of Cannabinoids fromUSDA Organic Industrial Hemp in a 2-Second Process with MeasurementsPerformed by Third Party ISO/IEC 17025 Accredited Cannabinoid-TestingLaboratories Raw Plant Material Extracted Plant Material Extract Percentby Percent by Percent by Percent by Cannabinoid Percent by CannabinoidPercent by Cannabinoid Mass Content Mass Content Mass Content CBDA 6.60%86.5% 0.00% 0.00% 0.92% 1.33% CBD 0.26% 3.41% 0.46%  100% 60.9% 88.2%THCA 0.18% 2.36% 0.00% 0.00% 0.00% 0.00% THC 0.00% 0.00% 0.00% 0.00%1.95% 2.82% CBGA 0.18% 2.36% * * 0.00% 0.00% CBG 0.00% 0.00% * * 1.40%2.03% CBCA 0.41% 5.37% * * 0.00% 0.00% CBC 0.00% 0.00% * * 3.91% 5.66%CBNA 0.00% 0.00% * * 0.00% 0.00% CBN 0.00% 0.00% * * 0.00% 0.00% Δ8THC0.00% 0.00% * * 0.00% 0.00% Total 7.63%  100% 0.46%  100% 69.0%  100%94.1% CBD Extraction Yield 98.3% CBD Decarboxylation Efficiency 100% THCExtraction Yield 100% THC Decarboxylation Efficiency CBDA =cannabidiolic acid CBCA = cannabichromenic acid CBD = cannabidiol CBC =cannabichromene THCA = tetrahydrocannabinolic acid CBNA = cannabinolicacid THC = tetrahydrocannabinol CBN = cannabinol CBGA = cannabigerolicacid Δ8THC = delta8-tetrahydrocannabinol CBG = cannabigerol * = nottested

TABLE 2 Gas-Phase Purification and Decarboxylation of Cannabinoids fromUSDA Organic Industrial Hemp in a 2-Second Process with MeasurementsPerformed by Third Party ISO/IEC 17025 Accredited Cannabinoid-TestingLaboratories Raw Plant Material Extracted Plant Material Extract Percentby Percent by Percent by Percent by Cannabinoid Percent by CannabinoidPercent by Cannabinoid Mass Content Mass Content Mass Content CBDA 6.44%85.4% 0.00% 0.00% 0.32% 0.41% CBD 0.11% 1.46% 1.00%  100% 69.9% 89.9%THCA 0.30% 3.98% 0.00% 0.00% 0.00% 0.00% THC 0.00% 0.00% 0.00% 0.00%2.33% 3.00% CBGA 0.27% 3.58% 0.00% 0.00% 0.00% 0.00% CBG 0.00% 0.00%0.00% 0.00% 1.37% 1.76% CBCA 0.42% 5.57% 0.00% 0.00% 0.00% 0.00% CBC0.00% 0.00% 0.00% 0.00% 3.61% 4.65% CBNA 0.00% 0.00% 0.00% 0.00% 0.00%0.00% CBN 0.00% 0.00% 0.00% 0.00% 0.19% 0.24% Δ8THC 0.00% 0.00% 0.00%0.00% 0.00% 0.00% Total 7.54%  100% 1.00%  100% 77.7%  100% 86.6% CBDExtraction Yield 99.5% CBD Decarboxylation Efficiency 100% THCExtraction Yield 100% THC Decarboxylation Efficiency CBDA =cannabidiolic acid CBCA = cannabichromenic acid CBD = cannabidiol CBC =cannabichromene THCA = tetrahydrocannabinolic acid CBNA = cannabinolicacid THC = tetrahydrocannabinol CBN = cannabinol CBGA = cannabigerolicacid Δ8THC = delta8-tetrahydrocannabinol CBG = cannabigerol

What is claimed is:
 1. A method to chemically-modify a cannabinoid,comprising: providing a composition comprising the cannabinoid, whereinthe cannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; contacting the composition withsufficient energy to convert the cannabinoid into carbon dioxide and amodified cannabinoid in a gas phase; contacting the modified cannabinoidwith a heat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate, wherein at least 85 percent of thecannabinoid is converted into the condensed cannabinoid per mole; andcollecting the liquid distillate.
 2. A method to chemically-modify acannabinoid, comprising: providing a composition comprising thecannabinoid, wherein the cannabinoid comprises a carboxyl group, and thecannabinoid is in a liquid phase or a solid phase; contacting thecomposition with sufficient energy to convert the cannabinoid intocarbon dioxide and a modified cannabinoid in a gas phase; contacting themodified cannabinoid with a heat sink to condense the modifiedcannabinoid into a condensed cannabinoid in a liquid distillate; andcollecting the liquid distillate, wherein the liquid distillatecomprises the condensed cannabinoid and cannabinol at a molar ratio ofgreater than 100:1.
 3. A method to chemically-modify a cannabinoid,comprising: providing a composition comprising the cannabinoid, whereinthe cannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; contacting the composition withsufficient energy to convert the cannabinoid into carbon dioxide and amodified cannabinoid in a gas phase; contacting the modified cannabinoidwith a heat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; collecting the liquid distillate,wherein the liquid distillate comprises ethanol; and evaporating theethanol to produce a product from the liquid distillate, wherein theproduct comprises the condensed cannabinoid at a concentration of atleast 55 percent by mass.
 4. A method to chemically-modify acannabinoid, comprising: providing a composition comprising thecannabinoid, wherein the cannabinoid comprises a carboxyl group, and thecannabinoid is in a liquid phase or a solid phase; contacting thecomposition with 2 kilojoules to 50 kilojoules of energy per gram of thecomposition to convert the cannabinoid into carbon dioxide and amodified cannabinoid in a gas phase; contacting the modified cannabinoidwith a heat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate.
 5. A method to chemically-modify a cannabinoid, comprising:providing a composition comprising the cannabinoid, wherein thecannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; contacting the composition with energy ata rate of less than 100 kilowatts of power per gram of the compositionfor a duration of less than 60 seconds to convert the cannabinoid intocarbon dioxide and a modified cannabinoid in a gas phase; contacting themodified cannabinoid with a heat sink to condense the modifiedcannabinoid into a condensed cannabinoid in a liquid distillate; andcollecting the liquid distillate.
 6. A method to chemically-modify acannabinoid, comprising: providing a composition comprising thecannabinoid and cellulose, wherein the cannabinoid comprises a carboxylgroup, and the cannabinoid is in a liquid phase or a solid phase;contacting the composition with sufficient energy to convert thecannabinoid into carbon dioxide and a modified cannabinoid in a gasphase; separating the modified cannabinoid in the gas phase from thecellulose; collecting the cellulose; contacting the modified cannabinoidwith a heat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate.
 7. A method to chemically-modify a cannabinoid, comprising:providing a composition comprising the cannabinoid, wherein thecannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; suspending a particle or a droplet of thecomposition in a gas phase, wherein the particle or the dropletcomprises the cannabinoid; contacting the composition with sufficientenergy to convert the cannabinoid into carbon dioxide and a modifiedcannabinoid in a gas phase; contacting the modified cannabinoid with aheat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate.
 8. A method to chemically-modify a cannabinoid, comprising:providing a composition comprising the cannabinoid, wherein thecannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; coating a heated surface with thecomposition at a surface-area-to-volume ratio of the composition that isgreater than 500 per meter; contacting the composition with sufficientenergy to convert the cannabinoid into carbon dioxide and a modifiedcannabinoid in a gas phase; contacting the modified cannabinoid with aheat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate.
 9. A method to chemically-modify a cannabinoid, comprising:providing a composition comprising the cannabinoid, wherein thecannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; directing the composition along a heatedpath having a length of at least 4 meters; contacting the compositionwith sufficient energy to convert the cannabinoid into carbon dioxideand a modified cannabinoid in a gas phase in the heated path; contactingthe modified cannabinoid with a heat sink to condense the modifiedcannabinoid into a condensed cannabinoid in a liquid distillate; andcollecting the liquid distillate.
 10. The method of claim 9, comprisingdirecting the composition along the heated path at a rate of at least 2meters per second.
 11. A method to chemically-modify a cannabinoid,comprising: providing a composition comprising the cannabinoid, whereinthe cannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; contacting the composition withsufficient energy to convert the cannabinoid into carbon dioxide and amodified cannabinoid in a gas phase; contacting the modified cannabinoidwith a heat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate, wherein both contacting the composition with the sufficientenergy and condensing the modified cannabinoid into the condensedcannabinoid are performed in less than 60 seconds.
 12. A method tochemically-modify a cannabinoid, comprising: providing a compositioncomprising the cannabinoid, wherein the composition has asurface-area-to-volume ratio of greater than 1000 per meter; thecannabinoid comprises a carboxyl group; and the cannabinoid is in aliquid phase or a solid phase; contacting the composition withsufficient energy to convert the cannabinoid into carbon dioxide and amodified cannabinoid in a gas phase; contacting the modified cannabinoidwith a heat sink to condense the modified cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate.
 13. A method to chemically-modify a cannabinoid, comprising:providing a composition comprising the cannabinoid, wherein thecannabinoid is cannabidiolic acid or tetrahydrocannabinolic acid, thecomposition comprises the cannabinoid at a concentration of at least 5percent by mass, and the cannabinoid is in a liquid phase or a solidphase; contacting the composition with sufficient energy to convert thecannabinoid into carbon dioxide and a modified cannabinoid in a gasphase; contacting the modified cannabinoid with a heat sink to condensethe modified cannabinoid into a condensed cannabinoid in a liquiddistillate, wherein at least 85 percent of the cannabinoid is convertedinto the condensed cannabinoid per mole; and collecting the liquiddistillate.
 14. A method to chemically-modify a cannabinoid, comprising:providing a composition comprising cannabidiolic acid, wherein thecomposition has a surface-area-to-volume ratio of greater than 1000 permeter, the composition comprises the cannabidiolic acid at aconcentration of at least 5 percent by mass, and the cannabidiolic acidis in a liquid phase or a solid phase; contacting the composition withsufficient energy to convert the cannabidiolic acid into carbon dioxideand gas phase cannabidiol; contacting the gas phase cannabidiol with aheat sink to condense the gas phase cannabidiol into liquid phasecannabidiol of a liquid distillate, wherein at least 85 percent of thecannabidiolic acid is converted into the liquid phase cannabidiol permole; and collecting the liquid distillate.
 15. The method of claim 14,comprising: contacting the composition with 2 kilojoules to 50kilojoules of energy per gram of the composition to convert thecannabidiolic acid into the carbon dioxide and the gas phasecannabidiol; and contacting the gas phase cannabidiol with the heat sinkless than 240 seconds after contacting the composition with the 2kilojoules to 50 kilojoules of energy per gram of the composition. 16.The method of any one of claims 1-15, wherein: the sufficient energy issufficient to maintain an average reaction rate for the conversion ofthe cannabinoid into the modified cannabinoid over a period of time; themodified cannabinoid is condensed at an average condensation rate forthe condensation of the modified cannabinoid into the condensedcannabinoid over a concurrent period of time; the average condensationrate is no less than 50 percent of the average reaction rate; theaverage reaction rate is no less than 50 percent of the averagecondensation rate; the period of time and the concurrent period of timeare chronologically identical; and the period of time and the concurrentperiod of time are at least 200 milliseconds and no greater than 5minutes.
 17. A method to purify a cannabinoid from a non-volatilechemical species, comprising: providing a composition comprising thecannabinoid and the non-volatile chemical species, wherein both thecannabinoid and the non-volatile chemical species are in a liquid phaseor a solid phase; contacting the composition with energy at a rate ofless than 100 kilowatts of power per gram of the composition for aduration of less than 60 seconds to convert the cannabinoid in theliquid phase or the solid phase into a vaporized cannabinoid in a gasphase without vaporizing the non-volatile chemical species; separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species; contacting the vaporized cannabinoid with a heat sinkto condense the vaporized cannabinoid into a condensed cannabinoid in aliquid distillate; and collecting the liquid distillate.
 18. A method topurify a cannabinoid from a non-volatile chemical species, comprising:providing a composition comprising the cannabinoid and the non-volatilechemical species, wherein both the cannabinoid and the non-volatilechemical species are in a liquid phase or a solid phase; contacting thecomposition with sufficient energy to convert the cannabinoid in theliquid phase or the solid phase into a vaporized cannabinoid in a gasphase without vaporizing the non-volatile chemical species; separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species; contacting the vaporized cannabinoid with a heat sinkto condense the vaporized cannabinoid into a condensed cannabinoid in aliquid distillate that comprises the condensed cannabinoid andcannabinol at a molar ratio of greater than 100:1; and collecting theliquid distillate.
 19. A method to purify a cannabinoid from anon-volatile chemical species, comprising: providing a compositioncomprising the cannabinoid and the non-volatile chemical species,wherein both the cannabinoid and the non-volatile chemical species arein a liquid phase or a solid phase; contacting the composition withsufficient energy to convert the cannabinoid in the liquid phase or thesolid phase into a vaporized cannabinoid in a gas phase withoutvaporizing the non-volatile chemical species; separating the vaporizedcannabinoid in the gas phase from the non-volatile chemical species;contacting the vaporized cannabinoid with a heat sink to condense thevaporized cannabinoid into a condensed cannabinoid in a liquiddistillate, wherein the method converts at least 85 percent of thecannabinoid into the condensed cannabinoid in the liquid distillate bymole; and collecting the liquid distillate.
 20. A method to purify acannabinoid from a non-volatile chemical species, comprising: providinga composition comprising the cannabinoid and the non-volatile chemicalspecies, wherein both the cannabinoid and the non-volatile chemicalspecies are in a liquid phase or a solid phase; contacting thecomposition with sufficient energy to convert the cannabinoid in theliquid phase or the solid phase into a vaporized cannabinoid in a gasphase without vaporizing the non-volatile chemical species; separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species; contacting the vaporized cannabinoid with a heat sinkto condense the vaporized cannabinoid into a condensed cannabinoid in aliquid distillate, wherein the vaporized cannabinoid is condensed intothe condensed cannabinoid less than 30 seconds after the cannabinoid isconverted into the vaporized cannabinoid in the gas phase; andcollecting the liquid distillate.
 21. The method of claim 20, whereineach of (i) contacting the composition with the sufficient energy, (ii)separating the vaporized cannabinoid in the gas phase from thenon-volatile chemical species, and (iii) contacting the vaporizedcannabinoid with the heat sink are performed in a total time of lessthan 30 seconds.
 22. A method to purify a cannabinoid from anon-volatile chemical species, comprising: providing a compositioncomprising the cannabinoid and the non-volatile chemical species,wherein both the cannabinoid and the non-volatile chemical species arein a liquid phase or a solid phase; suspending a particle or a dropletof the composition in a gas phase, wherein the particle or the dropletcomprises the cannabinoid; contacting the cannabinoid with sufficientenergy to convert the cannabinoid in the liquid phase or the solid phaseinto a vaporized cannabinoid in the gas phase without vaporizing thenon-volatile chemical species while the particle or the droplet issuspended in the gas phase; separating the vaporized cannabinoid in thegas phase from the non-volatile chemical species; contacting thevaporized cannabinoid with a heat sink to condense the vaporizedcannabinoid into a condensed cannabinoid in a liquid distillate; andcollecting the liquid distillate.
 23. A method to purify a cannabinoidfrom a non-volatile chemical species, comprising: providing acomposition comprising the cannabinoid and the non-volatile chemicalspecies, wherein both the cannabinoid and the non-volatile chemicalspecies are in a liquid phase or a solid phase; coating a heated surfacewith the composition at a surface-area-to-volume ratio of thecomposition that is greater than 500 per meter; contacting thecomposition with sufficient energy to convert the cannabinoid in theliquid phase or the solid phase into a vaporized cannabinoid in a gasphase without vaporizing the non-volatile chemical species while theheated surface is coated with the composition; separating the vaporizedcannabinoid in the gas phase from the non-volatile chemical species;contacting the vaporized cannabinoid with a heat sink to condense thevaporized cannabinoid into a condensed cannabinoid in a liquiddistillate; and collecting the liquid distillate.
 24. A method to purifya cannabinoid from a non-volatile chemical species, comprising:providing a composition comprising the cannabinoid and the non-volatilechemical species, wherein both the cannabinoid and the non-volatilechemical species are in a liquid phase or a solid phase; directing thecomposition along a heated path having a length of at least 4 meters;contacting the composition with sufficient energy to convert thecannabinoid in the liquid phase or the solid phase into a vaporizedcannabinoid in a gas phase without vaporizing the non-volatile chemicalspecies, wherein the contacting occurs in the heated path; separatingthe vaporized cannabinoid in the gas phase from the non-volatilechemical species; contacting the vaporized cannabinoid with a heat sinkto condense the vaporized cannabinoid into a condensed cannabinoid in aliquid distillate; and collecting the liquid distillate.
 25. A method topurify a cannabinoid from a non-volatile chemical species, comprising:providing a composition comprising the cannabinoid and the non-volatilechemical species, wherein both the cannabinoid and the non-volatilechemical species are in a liquid phase or a solid phase; grinding thecomposition to a surface-area-to-volume ratio of greater than 500 permeter; contacting the composition with sufficient energy to convert thecannabinoid in the liquid phase or the solid phase into a vaporizedcannabinoid in a gas phase without vaporizing the non-volatile chemicalspecies; separating the vaporized cannabinoid in the gas phase from thenon-volatile chemical species; contacting the vaporized cannabinoid witha heat sink to condense the vaporized cannabinoid into a condensedcannabinoid in a liquid distillate; and collecting the liquiddistillate.
 26. The method of claim 22, comprising: grinding thecomposition to a surface-area-to-volume ratio of greater than 500 permeter to produce particles of the composition; and suspending theparticles of the composition in the gas phase, wherein: the particles ofthe composition comprise the cannabinoid; and the cannabinoid iscontacted with the sufficient energy while the particles of thecomposition are suspended in the gas phase.
 27. The method of claim 22,comprising: suspending particles of the composition in the gas phase;and directing the particles of the composition along a heated pathhaving a length of at least 4 meters, wherein: the particles of thecomposition comprise the cannabinoid; and the cannabinoid is contactedwith the sufficient energy in the heated path.
 28. The method of any oneof claims 16-27, wherein: the sufficient energy is sufficient tomaintain an average vaporization rate for the conversion of thecannabinoid into the vaporized cannabinoid over a period of time; thevaporized cannabinoid is condensed into the condensed cannabinoid at anaverage condensation rate for the condensation of the vaporizedcannabinoid into the condensed cannabinoid over a concurrent period oftime; the average condensation rate is no less than 50 percent of thevaporization rate; the average vaporization rate is no less than 50percent of the average condensation rate; the period of time and theconcurrent period of time are chronologically identical; and the periodof time and the concurrent period of time are at least 200 millisecondsand no greater than 5 minutes.
 29. A method to chemically-modify acannabinoid, comprising: providing a composition comprising cannabinoidsand cellulose, wherein the cannabinoids comprise the cannabinoid, thecannabinoid comprises a carboxyl group, and the cannabinoid is in aliquid phase or a solid phase; suspending either a particle or a dropletof the composition in a gas phase, wherein the particle or the dropletcomprises the cannabinoid; contacting the composition with sufficientenergy to convert the cannabinoid into carbon dioxide and a modifiedcannabinoid in the gas phase while the particle or the droplet issuspended in the gas phase; separating the modified cannabinoid in thegas phase from the cellulose, wherein the separating occurs both (a)after converting the cannabinoid into the carbon dioxide and themodified cannabinoid in the gas phase, and (b) prior to contacting themodified cannabinoid with a heat sink; collecting the cellulose;contacting the modified cannabinoid with the heat sink to condense themodified cannabinoid into a condensed cannabinoid in a liquiddistillate; and collecting the liquid distillate.
 30. The method ofclaim 29, wherein contacting the composition with the sufficient energyto convert the cannabinoid into the carbon dioxide and the modifiedcannabinoid in the gas phase comprises contacting the composition withenergy at a rate of less than 100 kilowatts of power per gram of thecomposition for a duration of less than 60 seconds.
 31. The method ofclaim 29, wherein contacting the composition with sufficient energy toconvert the cannabinoid into the carbon dioxide and (ii) the modifiedcannabinoid in the gas phase comprises contacting the composition withat least 0.0003 and no greater than 0.04 kilowatt hours of energy pergram of the composition.
 32. The method of claim 29, comprisingcontacting the composition with a heated gas having a temperature of atleast 190 degrees Celsius and no greater than 250 degrees Celsius. 33.The method of claim 29, comprising contacting the composition with aheated surface having a temperature of at least 190 degrees Celsius andno greater than 250 degrees Celsius.
 34. The method of claim 29, whereinthe composition has a surface-area-to-volume ratio of greater than 1000per meter.
 35. The method of claim 29, comprising both contacting thecomposition with the sufficient energy and condensing the modifiedcannabinoid into the condensed cannabinoid in less than 60 seconds. 36.The method of claim 29, comprising directing the composition along aheated path having a length of at least 4 meters, wherein thecomposition is contacted with the sufficient energy in the heated path.37. The method of claim 36, comprising directing the composition alongthe heated path at a rate of at least 2 meters per second.
 38. Themethod of claim 29, wherein the cannabinoid is cannabidiolic acid, themodified cannabinoid is cannabidiol, and the condensed cannabinoid iscannabidiol.
 39. The method of claim 29, wherein the cannabinoid istetrahydrocannabinolic acid, the modified cannabinoid istetrahydrocannabinol, and the condensed cannabinoid istetrahydrocannabinol.
 40. The method of claim 29, comprising convertingat least 75 percent of the cannabinoid into the condensed cannabinoidper mole.
 41. The method of claim 29, comprising producing a liquiddistillate that comprises the condensed cannabinoid and cannabinol at amolar ratio of greater than 100:1.
 42. The method of claim 29,comprising producing a product from the liquid distillate, wherein theproduct comprises the condensed cannabinoid at a concentration of atleast 50 percent by mass.
 43. The method of claim 42, wherein the liquiddistillate comprises ethanol, and the method comprises evaporatingethanol to produce the product.
 44. The method of any one of claims29-43, wherein: the sufficient energy is sufficient to maintain anaverage reaction rate for the conversion of the cannabinoid into themodified cannabinoid over a period of time; the modified cannabinoid iscondensed at an average condensation rate for the condensation of themodified cannabinoid into the condensed cannabinoid over a concurrentperiod of time; the average condensation rate is no less than 50 percentof the average reaction rate; the average reaction rate is no less than50 percent of the average condensation rate; the period of time and theconcurrent period of time are chronologically identical; and the periodof time and the concurrent period of time are at least 200 millisecondsand no greater than 5 minutes.